


'Tis the Season

by existential1rony



Category: Chicago PD (TV)
Genre: Christmas Fluff, F/M, Friends to Lovers, Meet the Family, Slow Burn
Language: English
Status: Completed
Published: 2019-12-11
Updated: 2019-12-11
Packaged: 2021-02-25 20:28:25
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,098
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21751471
Author URL: https://archiveofourown.org/users/existential1rony/pseuds/existential1rony
Summary: Jay is perfectly content spending Christmas alone after the tumultuous year and few months he’s had. Did he honestly think Hailey would let him though? Would the tension between them become even more palpable if he spent the holidays with the Uptons? Maybe it’s just the push they need…
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 2
Kudos: 59





	'Tis the Season

**[Disclaimer: It pains me that I have to do this because I sadly still have hope in humanity and morals, but alas... It's been brought to my attention that some people have been stealing my stories. I ONLY post on FanFiction and ArchiveofourOwn... so if you come across anything of mine on Wattpad or any of the socials, please report it. Thank you! And to the offenders, be better people!]**

* * *

It's been a month and a half since Jay Halstead was shot and practically bleeding to death on an old, rusty warehouse floor. The first couple weeks of recovery had been a rough and a struggle, but his partner and best friend, Hailey Upton was consistently by his side every step of the way. Had he been grateful and in awe of her before, it had only amplified since then. He'll never forget the moment waking up in the hospital and the first eyes his came across were hers. It was poetic because hers were also the last ones he saw when he thought it was over, both in person and in his medically-induced dreams. It was only appropriate that she was also his focal point once the light returned. In the same regard, Hailey had never thanked the heavens more than when she saw Jay woke up and would eventually be okay. Her earth had completely shattered the day she thought she lost him, first to the kidnapping, then to the bullet wound. It was definitely an eye-opener for both parties of feelings they could no longer deny. They had yet to act on them, of course, with so much going on and both still holding onto a bit of insecurities; but their love for the other had become palpable, more than ever before.

Hailey helped Jay get through the first couple weeks he had to stay in the hospital, only leaving his side to work and help the team a few hours out of the day. She continued to help once he got the all-clear to return home too. She had slept over most nights those next few weeks, leaving only on the occasions Will said he would like to. In that time, it kind of placed Jay and Hailey in their own little bubble. They enjoyed the companionship of being around each other all the time without feeling the pressure to evaluate or discuss the reasoning. Most things they did in that time-span were activities of people who had been a couple for a while: Jay helping Hailey cook as much as the injury allowed, finding new shows to binge-watch all night, Hailey even helped him pick, put up, and decorate his Christmas tree. There had been a few serious talks in that span partially involving their feelings, but the one that had them close to admitting them and almost kissing, Hailey had pulled back. Jay had been slightly confused by it, but he decided to just let it go knowing she's been through a lot between almost losing him, _twice_ , to having already lost one partner she had been with. That was a lot for anyone to handle, let alone Hailey who feared she'd have to go through it a second time.

It had been a week and a half ago now that Jay got cleared to return to work on desk duty. This also meant that it was finally time for Hailey to start sleeping at her place again. Their time for playing house was over, much to both of their disappointment. Even though they're still seeing each other daily at work and have gotten together a couple nights for drinks, they miss the other terribly. Now if only they could admit it… It was two days until Christmas Eve and Voight had decided to give everyone the day off tomorrow with the crazy few months they've all had. Everyone was wrapping up in the bullpen for the day, excited to have the next few off. Vanessa was in her normal jovial mood and curious to see what holiday festivities her coworkers had planned.

"So what's everyone doing for Christmas this year? I'm excited, the Aunt and cousins I connected with a few years ago are flying in from LA. I haven't spent a holiday with family in Chicago ever!"

"Oh, that's great, Vanessa, how awesome. I'm going to drive up to see my sister, niece, and parents." Kim says from her desk.

"I'm flying my brother and sister in from Texas, so that will be a lot of fun. I can't believe he'll be legal drinking age soon. It's nuts." Kevin responds.

"Wow, that's crazy! Yea, I can't believe how old my nephew is getting either. Can't wait for him to smoke me at video games. What are you two doing?" Adam asks looking towards Hailey and Jay.

The two of them share a look wondering if he's assuming they'll be together, but choosing to ignore it. It seems the whole unit has caught on more to their harboring feelings as well.

"Oh um, my brothers are coming back to town, so going to spend it with their families and my parents. Nothing major." Hailey replies first.

"I'm looking forward to spending it quietly watching the Bulls game with some takeout. Maybe spike some eggnog since the doctors didn't let me drink for a while." Jay finally says.

Hailey gives him a perplexed look, wanting to say and ask a lot privately as Vanessa speaks. "You're spending Christmas alone?"

"Yeah, it hasn't been big in what's left of my family since my mom passed, and Will has some medical conference in Atlanta he'll be at all week." He replies trying to sound upbeat and avoid Hailey's gaze.

"Oh, that's too bad. Well, we should all get some drinks tonight to celebrate. I've only been here shortly, but I know it's not often we get an extended weekend off." Vanessa says.

Everyone agrees to meet up later in the night, getting back to wrapping up so they can finally start their time off. Jay and Hailey are the last to leave, shortly after the others, and remaining quiet until they get to Hailey's car. Jay is still on restricted driving, so she's been picking him up and dropping him home every day. Once they're finally in the confines of the car, she turns to look at him.

"Why didn't you tell me Will was going to be gone for Christmas?" She asks him softly.

"I just didn't think it was that big of a deal. If he was in town we'd probably still just watch the game and do nothing."

"Well, not this year. I'm not letting you spend it alone, you'll come with me."

"What?" he looks at her surprised. As much as he knows about Hailey and as close as they are, he still had yet to meet any of her family.

"Yup, you're coming with me. That's it, it's settled. Besides, it will be nice to kill two birds with one stone, saves me from stopping to visit you before I go to my parent's anyway."

"Hailey, you don't have to do this or worry about me, I'll be fine."

"Jay, after this past year, please never utter the phrase _I don't have to worry about you_ ever again." She jokes.

He chuckles back. "Alright, fair enough. But only if you're really sure? I don't want to impose."

"Are you kidding? My mom's a Greek who owns a restaurant, since her sisters moved away she'll be ecstatic to have another person to feed. I swear sometimes I feel like my brothers and me and her grandkids are never enough- that woman always wants more people around. Whereas me, I'd be perfectly content just watching the game just the two of us."

Jay smiles at her and gives her the look of awe he's had more and more as of late. Hailey realizing how that sounded, blushes, and quickly looks away from him to start the car.

"I can't wait to meet her, and the rest of your family, Hailey."

Jay responds softly, treading as lightly as he can. Hailey gives him a small smile back before pulling away from the curb, the dismal snow-covered Chicago streets suddenly looking much brighter.

* * *

Christmas day had finally arrived and Jay had been fretting over it for the past two days. What if Hailey's family didn't like him? Especially her brothers, she adores them. He switches his shirt for the fourth time, knowing Hailey will be arriving in the next few minutes to pick him up. He finally settles on a maroon button-down, hoping to show he can have holiday spirit. Lucky for him, Hailey is equally as nervous, just another sign of how on the same page they always are. As she walks up to his door she takes a deep breath before she knocks, it's now or never time. Once Jay pulls back the door they each look at the other in wonder. Hailey had chosen a casual red winter dress with black leggings, and added a little more makeup than normal.

"Wow, you look amazing!" Jay finally states after they spent a long beat staring at the other.

"You clean up pretty nicely yourself." Hailey responds, trying to play off the compliment, even though her heart is fluttering. "You ready to do this?"

"As long as your brothers go easy on me, I'm not at 100% yet to defend myself, it's hard enough keeping up with you." He jokes.

"Oh, they're harmless. I'm probably scarier than they are to be honest."

"I don't doubt that."

They smirk at each other, grabbing their coats to start heading out. Hailey's parents are about an hour out of the city. They spend the car ride laughing and her filling him in on small details of her family she may not have mentioned to him yet. There's not a whole lot, which surprises her because she can't believe just how much she's already revealed and opened up to Jay over the years. If you asked anyone else in the unit, or even some of her good friends, most wouldn't be able to tell you too much of anything regarding her family. But she's always been transparent with Jay, just like he is with her.

Once they arrive at her parent's door, Jay turns to Hailey one last time before she rings the bell, holding the wine he bought. "You sure just bringing this was fine? I don't want them to think I come empty-handed."

"Jay, the wine is fine. I told you not even to get that. Why are you so nervous? It's not like we're dating." She states, trying to hide her nerves as well.

They stare back at each other at her loaded statement, and right as Jay is about to respond they hear a shout from behind the door.

"Daddy, Aunt Hailey is here and she's with a boy." Her 10-year-old niece, Ella, yells right before opening the door for them.

Hailey and Jay get wide-eyed and are met with smiles from a bunch of Hailey's family members who had come to rush to the door at Ella's yelling. Hailey leans down to hug her niece and briefly lift her up.

"Hey munchkin, how've ya been?"

"Gross Aunt Hailey, I told you I'm too old now for you to still call me that!" the little girl responds sassily, amusing Jay because with her blonde hair, blue eyes, and personality she's like a dead ringer for little Hailey.

"Right. Sorry, I forgot. Ella, this is my friend, Jay. Jay this is my once adorable niece, Ella."

"Rude!" Ella replies to the dig, making Jay laugh further.

"Nice to meet you, Ella. I hate when your aunt calls me nicknames too."

"Yeah, yours are not nearly as endearing, Jay." Hailey says rolling her eyes watching Ella chuckle at his joke, secretly pleased he's winning over the near-preteen.

"Is he your boyfriend?"

Hailey is shocked at the direct question, but recovers quickly. "No, he's not. He's my partner."

"Oh, well he's cute." Ella says nonchalantly shrugging, before an alert pops up on her phone, distracting her and causing her to run out of the room before they can respond. Jay has to hold back a cough and his smirk as Hailey gives him her _don't even think of commenting_ face.

"Oh dear, she's teetering in that child-teenage years phase, sorry about that. Jay, it's so nice to finally meet you, I feel like I already know you with all the stories Hailey has told me."

" _Mom_!" Hailey seethes trying to hold down her embarrassment. She's really wishing now that she had bailed on them and told Jay they were watching the game just the two of them at his place.

Hailey's mom ignores her and continues on. She leans in to give Jay a hug, which he gladly accepts. "I'm Anna, Hailey's mom, and this is my husband, Dimitri. She steps back as Hailey's dad steps forward. Jay extends his hand to shake her dad's as Hailey hugs her mom. He wants to be sure to tread lightly with her father, knowing Hailey still isn't the closest with him after the issues he had in her childhood.

"The pleasure is all mine!" he smiles at her mom and nods at her dad. "Sir. Thanks for having me, I really appreciate it."

"Oh nonsense. Any friend of Hailey's is already family, we're glad to have you." Anna replies.

"We're glad to see you recovering so well." Dimitri finally speaks after giving Hailey a quick hug.

Jay and Hailey give each other a look, not really wanting to delve into _that_ of all things. Lucky for them before Jay gets a chance to respond her sister-in-laws come running over all excited to see her. It's been more than a few months. The girls hug ecstatically before introducing themselves to Jay. And right behind her brothers step into the foyer then.

"Hey, how's it going? I'm Danny, Hailey's oldest brother." He says turning to Jay.

"Good man, thanks. Jay, great meeting you." Jay introduces himself while shaking his hand.

"And I'm Adrian, middle child. Nice meeting you."

Jay nods and takes his hand too, Anna interrupting them all. "Alright, now that you've officially met everyone, let's get to the living room. Appetizers are almost ready."

Hailey's family quickly make their way into the other room at the mention of food, leaving Hailey and Jay hanging back for a second.

"This isn't so bad." Jay whispers to her as they start making their way.

"Yeah, easy for you to say, you're not related to them." Hailey rolls her eyes joking and they both laugh while entering the living room.

* * *

A couple hours later most of the group is still sitting in the living room, already pretty full from all the food Anna had made before the actual dinner. Jay thrilled to be getting his fill, not remembering the last time he had such a meal and the main course wasn't even out yet. Hailey watches him grab another small plate and chuckles to herself.

"Geez Jay, I'm gonna have to roll you out of here." She says quietly enough only for him to hear.

"Hailey, anytime you want to cook like this, I'll be over in a second."

"Pff, don't hold your breath. I haven't made my mom's elaborate meals in years."

"You cooked for me all last month, what are you talking about?"

"Yeah, but that was different, I was doing it for you." He quirks his eyebrow up at her as she lets that slip, so she quickly tries to save herself. "I mean, you know, cause you were recovering and all. You know what I mean…" she says feebly.

Jay smiles internally and decides to drop it for her, focusing instead on her little nephew, Timmy, whose been occupying himself in the corner with his trucks most of the time. Jay nods over to him. "He's a quiet kid, I think I've heard him say two sentences all night."

"Yea, he's really shy now ever since my brother has had to start traveling for work more. It kills Danny every time he has to leave. Timmy's such a sweetheart though, he used to follow me around everywhere since he was a baby… but lately they can't seem to get him to open up. He just likes playing alone. We're hoping it's just a stage." Hailey says a little sadly.

"Hmm, reminds me of a little boy I used to know." Jay replies winking at her. "Mind if I ditch you for a bit?"

Hailey smiles and raises her hand gesturing towards Timmy. "Have at it."

Jay stands up from the couch and heads over to kneel down by the tree where Timmy is playing. Timmy barely glances up from his collection of toy trucks and cars. Jay doesn't let it deter him though. "Hey buddy! You know, I was a soldier when I was younger and used to drive in one of these all the time." He says while picking up the army tanker.

Timmy's head pops up instantly then and he exclaims, "You did?" in such an excited way that only a little kid could.

"Yeah I did, you want me to tell you how each part operates?" Jay asks as he fully sits on the floor with him now.

Timmy nods his head eagerly at Jay as Hailey watches on in shock and admiration. If her heart wasn't full of Jay already, this for sure set it over the edge. She hasn't seen her nephew this happy in almost a year. A couple minutes later her sister-in-laws, Steph and Renee, have caught on and made their way to sit with Hailey on the couch, watching in awe as well.

"Hailey, if you don't jump his bones by dinner, I'm divorcing your brother and doing it myself!" Steph, Timmy's mother jokes.

Hailey blushes. "Stop, we're just friends."

"Yea, and I'm the Virgin Mary!" Renee chimes in.

"Oh my God, would you look how happy Timmy looks? He barely even plays with Ella anymore." Steph says almost tearing up.

The girls stare on watching Jay play with Timmy until Anna calls them all into the dining room for dinner. Everyone now in shock to see the friend Jay made. Jay stands up and Timmy follows.

"Mommy, can I sit next to Jay?" Timmy asks.

Steph looks to Jay and Hailey to see if it's okay and they both just smile and nod. "Sure hun, c'mon let me grab your apple juice."

Hailey waits for everyone to walk into the dining room before speaking again, turning to Jay. "Wow, I am impressed!"

Jay just shrugs grinning. "I'm a man of many hidden talents, Hailey."

He whispers it close to her hear, knowing exactly what he's doing. Hailey knows for sure now that Jay Halstead is going to be the death of her.

* * *

"So Jay, how the heck do you put up with my annoying little sister day in and day out? I can't imagine having to be stuck in a van or something with her for hours on end. And watch when she orders the beans for her hotdogs." Adrian jokes while they're all eating dinner.

"Shutup, Ri! You're still such a child!" Hailey responds, everyone cracking up at Hailey's exasperation.

"Oh, it's not that bad. But when she gets the onions on it however, phew…" Jay plays along.

"JAY! Do not encourage him!"

"I'm kidding! Hailey's an amazing partner. We should all wonder how she puts up with _me_ to be honest. I'm sure I'd be dead in a ditch somewhere at this point if it wasn't for her…" Jay says, quickly realizing how close-to-home that sounds as Hailey's face turns white and everyone looks at them sympathetically. He tries to backtrack and lift the mood. "I just mean, she's always there for me, you know? She's a great cop and even better person."

Hailey smiles in appreciation, fully realizing Jay just won over her whole family in less than thirty seconds. "You're not so bad yourself, Halstead."

Anna shares a knowing look and smile with her daughter-in-laws before changing the subject, figuring her daughter would want the spotlight off of her and Jay. They all carry on amicably while they finish eating and try to digest. After dinner, the girls all got up to make a start at cleaning the dishes and gathering dessert. Dimitri had to show Adrian something in his shop, which left just Jay and Danny alone briefly.

"You smoke cigars, Jay?" Danny asks him.

"Not often, but I enjoy one every now and then."

"C'mon then, I have some Cubans." Danny nods for him to follow him out to the front porch.

The two men grab their coats and try to brace the cold. They light their cigars and quietly stare off into the dark night for a bit. Danny breaks the silence first.

"Thanks for hanging with Timmy. I haven't seen him so excited for a person since he used to go nuts anytime Hailey would visit. Her being a cool aunt _and_ a cop made her his hero. But he hasn't even been that way with her in a while."

"Oh, it's no problem. He seems like a great kid. Reminds me a little of me at his age. He'll come out of his shell again soon."

"I hope so…" Danny replies and the conversations drips off for a bit.

"So I have to say, even though Hailey speaks so highly of you, I'm still kind of in shock she brought you here." Danny continues.

"What do you mean?" Jay says generally curious, and a little trepidatious. Up until this point he had thought things were going well and that everyone liked him.

"It's just Hailey _never_ brings a guy home, at least not since before she joined the academy. And even then the only one was her college sweetheart."

"She didn't even let you guys meet Garrett?" Jay asks, referring to Hailey's partner and boyfriend who got killed by Booth.

"To be honest, we didn't even know he existed until after he passed away. She never mentioned him before. Of course, she was a wreck after, but she kept her relationship with him away from us. Which was odd because as much as we fight like cats and dogs and tease her all the time, she's always seeking our approval. Beauty of being older brothers I guess."

"Wow, yea I had no idea. I just assumed you guys must have known him, it sounded like she really loved him."

"I'm sure she did, but whatever it was he was never important enough for her to include us, even as her partner. You however, I feel like I know more about you than I do some of my good friends. She's been talking about you since you guys first got paired up… sure, some of it is frustrations, but I can tell she really cares about you."

Jay stares at him astonished. He knows he means a lot to Hailey, it's been even more evident the past couple of months, but she just always seemed to pull back whenever they got closer. Now that it's all been confirmed to him though, he's determined to do something about it once and for all.

"I care a lot about her too." Jay replies assuredly.

"I know… I can see the way you look at her. Listen, I'm not telling you all this as that 'older brother warning' or anything, I just know my sister and she's not always the most vocal in how she feels. But, she deserves someone like you to be with and look after her. She told me about that incident in the van over spring where you saved her life. And it also sounds like she lets you in, she doesn't even do that for us always. If you want to be with her- and I think you do because what man in their right mind not in love would come to a house full of crazy Greeks at Christmas?- don't let her give you no for an answer anymore!"

Jay just laughs. "Wow, when Hailey told me her oldest brother didn't hold back, she really meant it."

Danny laughs back. "Sometimes you just can't with a sister like Hailey."

"Yea, I'll bet. Thanks man, I really appreciate it. She really is my whole world." Jay responds, reaching his hand out to shake his.

"Yea, good luck! You're gonna need it!.. I'm kidding, slightly."

"Don't I know it!?"

The two guys laugh again and finally make their way back in. Once they step inside they see Hailey waiting and eyeing them up curiously. Danny walks over to her and kisses her cheek before making his way back to the kitchen.

"What did you guys talk about?"she questions Jay.

"Oh nothing much. Just how shitty the Bears and Hawks have been recently."

Hailey eyes him up, knowing full well he's lying. "Mhmm."

Jay just smirks and rubs his stomach. "So when's dessert?"

* * *

After an eventful night, Hailey and Jay have finally made it back to his place. Her family kept serving food until well into the night, so it was well past midnight when they got back to Chicago. The drive home was relatively quiet, both reflecting on everything that had transpired the past few hours.

"So I think you guys have spoiled me for life now. I'm not going to want to do a holiday any other way. I also don't think I'll be able to eat again for a week." Jay says as they make their way over to his couch and plop.

"You know what they say, Jay, be careful what you wish for!"

"Well right now, I'm wishing to get this belt off." He jokes as he yanks it out and throws it on the floor, making Hailey laugh.

Jay turns on a reair of the Bulls game and the two of them sit back with their heads close together. The glow from the TV and the Christmas tree they put up together giving off the only light in the living room. After a little while Hailey finally works up the courage to speak her thoughts.

"So you ever gonna tell me what you and Danny really talked about?"

"Just how much we care for each other." Jay admits.

Hailey is taken back a second by his brutal honesty. "What?"

"Yeah, he told me how much he thinks you care about me and that he could tell I cared about you too. So I told him you were my whole world…"

"Jay…" she whispers softly, unsure of what else to say.

He turns his head to stare into her eyes and grabs one of her hands in his. "Hailey, look, I'm not going to push you into doing or admitting anything. I know everything that happened last month made you want your guard up even more, and I don't blame you. I can't imagine what I'd feel if the situations were reversed. I can't imagine the thought of thinking I lost you. It would kill me. But, I just want you to know that when you are ready, I'm here and I'm not going anywhere…"

Hailey feels tears well in her eyes and she looks down at their joined hands, trying to focus on anything else as she gathers her thoughts. After a couple minutes she finally speaks, deciding it's finally time to rip the bandaid. Life is too short and they sadly had both learned that unfortunately way too much.

"I'm sorry I pulled away when we almost kissed a couple of weeks ago. It's just my feelings for you take up every thought and fiber of my being and that scares the hell out of me, Jay. I've never felt this way about anyone before, and the risks and complications of our job just make it all that much scarier. I can't go through losing someone again…"

"Hailey…" Jay starts to say thinking he'll have to convince her more, but she continues on.

"…But I want to try, because what's scarier than the thought of losing you is the thought of never even getting to be with you. I'm in love with you, Jay, and tonight, seeing you with my family, with Timmy, made me realize I don't want to run from it anymore. I want to run toward it."

She finally looks back up at him to see him grinning from ear to ear, with his silly expression she's noticed he only has for her.

"I love you too, Hailey, so much! I think I always have." He says softly as he moves his hand to stroke her cheek.

She grins and responds in the only way she should have done years ago. She grabs his face in her hands and pulls him down into a fiery kiss. The moment seems to go on forever, their kiss getting more and more heated until finally they have to break apart to catch their breath. When they do they're both grinning like teenagers.

"Mmm, well that was certainly worth the wait." Jay says, his voice huskier than normal.

She gives him another quick peck. "I just remembered I didn't give you your Christmas gift yet."

"What? I thought we said we were just going to treat ourselves to a nice dinner. What gift?"

She wraps her arms around his neck and pulls him down the couch with her. "It's under my dress. You're just going to have to _unwrap_ it to find out…" she whispers back to him.

Jay's eyes go wide, but he's never been more excited for a challenge in his life. "Merry Christmas to me!"

He quickly goes back to kissing her, wrapping his arms tightly around her as his hands start to explore. Their first Christmas together goes long into the night. It was the best gift either one of them could ever imagine…

* * *

_[A/N: Just a warm, light, and fuzzy holiday fare one-shot. Hope you enjoy reading it as much as I did writing it. I have plans to update/epilogue my last multi-chapter, but outside of that I have no other story agenda yet. So if there's an Upstead plot or something you'd like to see explored, let me know. I'm always open to another idea. Thanks for continuing to read these and hope you all have Happy Holidays! The show can't return soon enough.]_


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